For digital nomads, work is where the laptop is

MEDELLIN, Colombia – Gwendolyn DaSilva rises at 5 a.m. to teach English to Chinese children from a small office just off her kitchen in Colombia. Through an online teaching portal, she gives one-hour private lessons for about four hours to children ages 5 to 12, and then she walks to a coffee shop to spend most of the day blogging about Medellin and travel.

For nearly 15 years, DaSilva was a corporate marketing executive in London, but she found herself at a crossroads during a rough patch in her life.

“I didn’t know what to do, so I hired a life coach,” DaSilva said. “We went through several months of work and came to the conclusion that the best thing to do would be to take a year off and travel around the world.”

The 41-year-old native of Glasgow, Missouri, gave up her six-figure salary and spent a year teaching English in South Korea. Now, in Medellin, she’s part of a community of digital nomads who have moved their lives and work to distant locales – often sun-soaked and always with a solid digital infrastructure – to take advantage of a lower cost of living.

Many of the nomads call it “geoarbitrage,” a term popularized by the Tim Ferriss book “The 4-Hour Workweek: Escape 9-5, Live Anywhere, and Join the New Rich.”

NomadList, a crowdsourced database, has determined that a single person living in Canggu, Bali, Indonesia – among the top-ranked places for digital nomads on the site – can rent a private room in a hotel in the center of town and eat three meals a day for about $1,100 a month. Medellin is cheaper, with a monthly cost of living of about $900.

Travelers rely on a budding cottage industry of companies such as Unsettled, Remote Year, Hacker Paradise and Wanderist Life to help navigate the logistics of working in a foreign country, although not to find the work. Most require that freelance work or clients be in place first.

DaSilva came to Medellin with Unsettled, which for a month offered co-working space, cultural tours and workshops. It also found her an apartment.

“I was able to build a community here quite quickly . . . much quicker here than I ever did in my other places,” she said. She finishes teaching at 9 a.m., and then her day is free. She said her plans for the week included touring a sloth sanctuary outside the city and helping a craft brewer bottle beer.

Teachers who work for VIPKID, the online teaching company based in Beijing, are paid $14 to $20 an hour, depending on how they are rated in an “apples” scale by the students and their parents. Too many low ratings, and the company will require that the teacher receive additional training, or it might even fire the teacher. DaSilva said that she likes having the flexibility to choose how much she works and that a lot of credentialing wasn’t needed.

Colombia, Medellin in particular, is rapidly becoming a hub because of a favorable currency exchange, affordable health care, springlike weather and a time zone that makes working with American clients easier than in some other parts of the world. (DaSilva does have emergency health insurance.)

The city is trying to shed its reputation for drug violence. Last year, it was notably not on Business Insider’s list of the 50 most violent cities in the world. (New Orleans, Baltimore and St. Louis were listed.)

“The successful model for a digital nomad [includes being] able to bill the U.S., so if you need to communicate with people you’re billing, there’s no question that South America has unique benefits,” said Todd Morrill, a Baltimore native and Web developer who lives in Colombia. Morrill began a digital-nomadic life in 2002, but about a decade later, he settled in Medellin, working legally under a nonresident visa. In 2017, he claimed Colombian residency.

In a variation on the footloose lifestyle, some people are turning less nomadic, staying for months – and in some cases, years – and embedding themselves in communities of like-minded workers.

After six months in Santiago, Chile, Dustin Laverick came to Medellin with plans to continue building up his online marketing company. Laverick, who is German and in his late 30s, knows the digital-nomadic life well. But he doesn’t think he fits the usual description.

“The thing that pops into my head when you say ‘digital nomad’ is one who is literally going somewhere new for two to three weeks or a month, always on the move and always traveling,” he said. “That’s the word ‘nomad.’ I don’t think a nomad would sit in one place for six months.”

Yet that is happening. And some countries are changing visas to accommodate those who linger. Thailand approved the “Smart Visa,” what many call the digital nomad visa, which allows knowledge workers and entrepreneurs to live and work there for four years without having to apply for a work permit.

In late 2017, Colombia streamlined its visa classifications into three categories: migrant, visitor and resident. Depending on the type of work involved, Colombia’s migrant visa is good for up to three years, and a visitor visa for up to six months in a calendar year. Digital nomads from the United States and Europe can still enter the country and work on a tourist stamp for 90 days, and then they have the option to renew for another 90 days.

Even though the digital nomadic lifestyle has grown more appealing, it comes with legal ambiguity and ethical controversy. Many of these workers subscribe to what is known as “flag theory,” finding places with favorable tax policies to incorporate their online businesses and living in countries with low or no sales or tourist taxes.

However, U.S. citizens are still legally obligated to pay federal taxes, even if they claim residency in another country. DaSilva finds her tax situation to be continually complicated. “It’s a gray area,” she said, when a U.S. citizen, working in another country on a tourist visa, is employed by a Chinese company and gets paid in U.S. dollars.

Although local residents are generally welcoming, expatriates and digital nomads tend to stick together.

“I don’t think there’s an incentive for digital nomads to get involved in local politics and initiatives. Maybe they get on Tinder, but that’s about it,” said Ximena Restrepo, a Colombian who started Catalyst Weekly, an events website geared toward digital nomads and expatriates in Medellin.

With most digital nomads working in the knowledge economy, officials in Medellin would like to get them plugged into the local economy. But it can be a tough sell.

Eddie Arrieta, founder of Espacio, a business incubator, and owner of several start-up businesses, said digital nomads, though serious entrepreneurs, are reluctant to give up the mind-set of not needing a normal 9-to-5 job when they live in a low-cost environment.

“I think the moment start-ups here can say, ‘Hey, it’s the same salary here you can get there,’ that’s the moment where they say: ‘I no longer need to be a digital nomad. I have a job in Medellin. I just live in Medellin; that’s what I do,’ ” Arrieta said.

There are many reasons to stay in one spot. DaSilva pointed out a big one: Constant travel is tiring.

“I think for most people, certainly as they get older, that kind of schedule is exhausting and not sustainable,” DaSilva said. “You can commit to a set period, but I think after that, most digital nomads are committing to staying as long as the visa will allow them to stay in the country.”

Then there’s the big question of home. As in, when do you go back to your home country, if ever?

Laverick’s long-term goal is to return to Europe, so he can be closer to his family and eventually “graduate from nomad life.” But he said that won’t happen in the near future.

“I’m a person who leaves making decisions until the last moment,” Laverick said. “Which probably explains why I’m in this lifestyle.”